Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:02 UTC |
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Update date | 2020-09-17 15:41:18 UTC |
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Primary ID | FDB001613 |
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Secondary Accession Numbers | |
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Chemical Information |
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FooDB Name | Allantoin |
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Description | Allantoin, also known as glyoxyldiureide or 5-ureidohydantoin, belongs to the class of organic compounds known as imidazoles. Imidazoles are compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms. An imidazolidine-2,4-dione that is 5-aminohydantoin in which a carbamoyl group is attached to the exocyclic nitrogen. Allantoin is an extremely weak basic (essentially neutral) compound (based on its pKa). Allantoin exists in all living species, ranging from bacteria to humans. Outside of the human body, Allantoin is found, on average, in the highest concentration within milk (cow) and borages. Allantoin has also been detected, but not quantified in, several different foods, such as sour cherries, italian sweet red peppers, longans, sweet bay, and lambsquarters. This could make allantoin a potential biomarker for the consumption of these foods. Allantoin is a potentially toxic compound. |
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CAS Number | 97-59-6 |
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Structure | |
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Synonyms | Synonym | Source |
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(2,5-Dioxo-4-imidazolidinyl)urea | ChEBI | 2,5-Dioxo-4-imidazolidinyl-urea | ChEBI | 4-Ureido-2,5-imidazolidinedione | ChEBI | 5-Ureido-2,4-imidazolidindione | ChEBI | 5-Ureidohydantoin | ChEBI | Glyoxyldiureide | ChEBI | N-(2,5-Dioxo-4-imidazolidinyl)urea | ChEBI | (S)-Allantoin | HMDB | 5-Ureido-hydantoin | HMDB | 5-Ureidohydrantoin | HMDB | Alantan | HMDB | Allantol | HMDB | Alloxantin | HMDB | AVC/Dienestrolcream | HMDB | Cordianine | HMDB | D00121 | HMDB | Fancol toin | HMDB | Glyoxyldiureid | HMDB | Glyoxylic diureide | HMDB | Psoralon | HMDB | Sebical | HMDB | Septalan | HMDB | Sween brand OF allantoin | HMDB | Herpecin-L | HMDB | HerpecinL | HMDB | Reed and carnrick brand OF allantoin | HMDB | Woun'dres | HMDB | Allantoin sween brand | HMDB | Campbell brand OF allantoin | HMDB | Allantoin campbell brand | HMDB | Herpecin L | HMDB | (+/-)-allantoin | biospider | 1-(2,5-dioxoimidazolidin-4-yl)urea | biospider | 2,5-Imidazolidinedione, 4-ureido- | biospider | 4-ureido-2,5-Imidazolidinedione | biospider | 5-Ureido-2,4-imidazolidindion | biospider | 5-ureido-Hydantoin | biospider | Allantoin (8CI) | biospider | Allantoin (jan/usp) | biospider | Allantoin [usan:ban] | biospider | Campbell brand of allantoin | biospider | Cutemol emollient | biospider | DL-allantoin | biospider | Glyoxylic(acid) diureide | biospider | Hemocane | biospider | Herpecin l | biospider | Herpecin-l | biospider | Herpecinl | biospider | Hydantoin, 5-ureido- | biospider | N-(2,5-dioxoimidazolidin-4-yl)urea | biospider | N-[2,5-dioxoimidazolidin-4-yl]urea | biospider | Paxyl | biospider | Reed & carnrick brand of allantoin | biospider | Skin strategies for men-soothing moisturizer | biospider | Sween brand of allantoin | biospider | Uniderm a | biospider | Urea, (2, 5-dioxo-4-imidazolidinyl)- | biospider | Urea, (2,5-dioxo-4-imidazolidinyl)- | biospider | Urea, (2,5-dioxo-4-imidazolidinyl)- (9CI) | biospider | Urea, N-(2,5-dioxo-4-imidazolidinyl)- | biospider | Ureidohydantoin | biospider |
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Predicted Properties | |
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Chemical Formula | C4H6N4O3 |
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IUPAC name | (2,5-dioxoimidazolidin-4-yl)urea |
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InChI Identifier | InChI=1S/C4H6N4O3/c5-3(10)6-1-2(9)8-4(11)7-1/h1H,(H3,5,6,10)(H2,7,8,9,11) |
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InChI Key | POJWUDADGALRAB-UHFFFAOYSA-N |
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Isomeric SMILES | NC(=O)NC1NC(=O)NC1=O |
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Average Molecular Weight | 158.1154 |
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Monoisotopic Molecular Weight | 158.043990078 |
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Classification |
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Description | Belongs to the class of organic compounds known as imidazoles. Imidazoles are compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Azoles |
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Sub Class | Imidazoles |
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Direct Parent | Imidazoles |
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Alternative Parents | |
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Substituents | - Imidazole
- Isourea
- Azacycle
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Carboximidamide
- Carboximidic acid derivative
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Imine
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Industrial application: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | 239 oC | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 5.26 mg/mL | YALKOWSKY,SH & HE,Y (2003) |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-0006-9200000000-5ad052308edfab7b8c5f | 2014-09-20 | View Spectrum | GC-MS | Allantoin, non-derivatized, GC-MS Spectrum | splash10-0uds-0911000000-d6d990e16a15b9f27262 | Spectrum | GC-MS | Allantoin, non-derivatized, GC-MS Spectrum | splash10-0udi-0920000000-abb5512bfc08cbdd004f | Spectrum | GC-MS | Allantoin, non-derivatized, GC-MS Spectrum | splash10-0f79-0900000000-bf39d4fc494ccd722796 | Spectrum | GC-MS | Allantoin, 5 TMS, GC-MS Spectrum | splash10-00kr-4911230000-f2112ac79e45fb821ab6 | Spectrum | GC-MS | Allantoin, 4 TMS, GC-MS Spectrum | splash10-0f8i-3933100000-45367e01790bfc8afd6e | Spectrum | GC-MS | Allantoin, 3 TMS, GC-MS Spectrum | splash10-0zfr-4951100000-88808e71aea4d5ad7885 | Spectrum | GC-MS | Allantoin, non-derivatized, GC-MS Spectrum | splash10-0006-9100000000-5f4cd23ea44234e5a455 | Spectrum | GC-MS | Allantoin, non-derivatized, GC-MS Spectrum | splash10-0006-9100000000-c9c0d8a7f1e5f105a9c3 | Spectrum | GC-MS | Allantoin, non-derivatized, GC-MS Spectrum | splash10-0uds-0911000000-d6d990e16a15b9f27262 | Spectrum | GC-MS | Allantoin, non-derivatized, GC-MS Spectrum | splash10-0f79-0900000000-bf39d4fc494ccd722796 | Spectrum | GC-MS | Allantoin, non-derivatized, GC-MS Spectrum | splash10-00kr-4911230000-f2112ac79e45fb821ab6 | Spectrum | GC-MS | Allantoin, non-derivatized, GC-MS Spectrum | splash10-0f8i-3933100000-45367e01790bfc8afd6e | Spectrum | GC-MS | Allantoin, non-derivatized, GC-MS Spectrum | splash10-0zfr-4951100000-88808e71aea4d5ad7885 | Spectrum | Predicted GC-MS | Allantoin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0296-9700000000-45ea72c639ca30cd7783 | Spectrum | Predicted GC-MS | Allantoin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Allantoin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-02t9-8900000000-bb0a5fee22239a104e6f | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-03dj-9000000000-09992debd5f3d399b902 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-01oy-9000000000-8fe7df22b2abb81b934a | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (Unknown) , Positive | splash10-0006-9100000000-08b1881abaf98821d201 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positive | splash10-0006-9100000000-297710f62f9699946151 | 2012-08-31 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-066r-0900000000-4e30eec1c2a8c4cb7fa8 | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-014i-5900000000-0e0e6cbea70e14292a57 | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-006w-9000000000-d53fc563af9567f05b8a | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-066r-0900000000-4e30eec1c2a8c4cb7fa8 | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-014i-5900000000-0e0e6cbea70e14292a57 | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-006w-9000000000-d53fc563af9567f05b8a | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-066r-0900000000-4e30eec1c2a8c4cb7fa8 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-014i-5900000000-0e0e6cbea70e14292a57 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-006w-9000000000-d53fc563af9567f05b8a | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-066r-0900000000-4e30eec1c2a8c4cb7fa8 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-014i-5900000000-0e0e6cbea70e14292a57 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-006w-9000000000-d53fc563af9567f05b8a | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03k9-9600000000-775f532f9c5d9acd1ee6 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01vo-9400000000-a4e69e926b530e953cc3 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-4c973a5209a8104a49e3 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03k9-9600000000-775f532f9c5d9acd1ee6 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01vo-9400000000-a4e69e926b530e953cc3 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-4c973a5209a8104a49e3 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03k9-9600000000-775f532f9c5d9acd1ee6 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01vo-9400000000-a4e69e926b530e953cc3 | 2015-05-27 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 13C NMR Spectrum (1D, 125 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 400 MHz, H2O, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | Not Available |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C01551 |
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Pubchem Compound ID | 204 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 15676 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB00462 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | ALLANTOIN |
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BIGG ID | Not Available |
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KNApSAcK ID | C00007468 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Allantoin |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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Anti-dandruff | | An agent that reduces the production or flaking of dandruff, treating scalp conditions like seborrheic dermatitis, psoriasis, and eczema, by inhibiting fungal growth and inflammation, promoting a healthy scalp. | DUKE | Anti-inflammatory | 35472 | An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis. | DUKE | Anti-oxidant | 22586 | An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects. | DUKE | Anti peptic | | An agent that inhibits the action of pepsin, reducing stomach acid and digestive enzyme activity. Therapeutically, it is used to treat gastrointestinal disorders, such as peptic ulcers and gastroesophageal reflux disease (GERD), by protecting the mucous lining and promoting healing. | DUKE | Anti-psoriac | 52217 | An agent that reduces psoriasis symptoms, commonly used in managing plaque psoriasis, scalp psoriasis, and other inflammatory skin conditions, by inhibiting cell growth, reducing inflammation, and modulating the immune system. | DUKE | Anti radicular | | An agent that relieves inflammation or irritation of the nerve root of a tooth, reducing pain and discomfort. Its biological role is to target and alleviate radicular pain, with therapeutic applications in endodontics and key medical uses in root canal treatments and tooth sensitivity management. | DUKE | Anti ulcer | 49201 | An agent that reduces stomach acid and protects the mucous lining, preventing ulcer formation. It is used to treat conditions like gastroesophageal reflux disease (GERD), peptic ulcers, and Zollinger-Ellison syndrome, promoting healing and relieving symptoms. | DUKE | Immunostimulant | 50847 | An agent that stimulates the immune system, enhancing its response to infections and diseases. Therapeutically, it boosts the body's natural defenses, commonly used to treat immunodeficiency disorders, prevent infections, and support cancer treatment, as well as manage chronic conditions like hepatitis and HIV. | DUKE | Keratolytic | | An agent that breaks down excess skin cells, removing warts and other lesions. It plays a biological role in regulating epidermal growth. Therapeutically, it's used to treat hyperkeratotic conditions. Key medical uses include managing warts, calluses, and ichthyosis, promoting skin smoothing and renewal. | DUKE | Sunscreen | 52217 | A topical agent that blocks UV radiation, preventing skin damage and reducing the risk of skin cancer. Its therapeutic applications include protection against sunburn, photoaging, and photodermatoses. Key medical uses include prevention of melanoma, basal cell carcinoma, and squamous cell carcinoma, as well as management of photosensitive disorders. | DUKE | Suppurative | | An agent that promotes the formation of pus, facilitating the removal of infectious material. Its biological role involves enhancing the body's natural defense mechanism. Therapeutically, it is used to treat infections, abscesses, and wounds, promoting drainage and healing. Key medical uses include managing purulent discharge, infected lesions, and septic conditions. | DUKE | Vulnerary | 73336 | An agent that promotes wound healing, tissue repair, and skin regeneration. It facilitates the biological process of recovery, reducing inflammation and infection. Therapeutically, vulneraries are used to treat cuts, burns, ulcers, and other skin injuries, supporting the body's natural healing mechanisms and minimizing scarring. | DUKE |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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